Acetonitrile → 3-Amino-3-(6-methoxypyridin-3-yl)prop-2-enenitrile

Participants

Reaction Steps

A solution of 0.258 ml (1.844 mmol) diisopropylamine in dry THF (1.5 ml) was cooled to −70° C. under inert gas atmosphere, and 1.152 ml (1.844 mmol) n-butyllithium (1.6 M solution in hexanes) were added dropwise. Then, a solution of 85.6 μl (1.627 mmol) acetonitrile in dry THF (1.5 ml) was slowly added over 10 min. The resulting solution was stirred for further 30 min at −70° C. before a solution of 150 mg (1.085 mmol) 2-methoxypyridine-5-carbonitrile in dry THF (1.5 ml) was added. The mixture was allowed to warm to room temperature and stirred for 1 h before water (2 ml) was added slowly. The mixture was extracted several times with dichloromethane (50 ml). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to yield 188 mg (99% of th.) of the crude title compound which was used in the next step without further purification.

Provenance & Evidence